Abstract
Willow (Salix spp.) is well known as a source of medicinal compounds, the most famous being salicin, the progenitor of aspirin. Here we describe the isolation, structure determination, and anti-cancer activity of a cyclodimeric salicinoid (miyabeacin) from S. miyabeana and S. dasyclados. We also show that the capability to produce such dimers is a heritable trait and how variation in structures of natural miyabeacin analogues is derived via cross-over Diels-Alder reactions from pools of ortho-quinol precursors. These transient ortho-quinols have a role in the, as yet uncharacterised, biosynthetic pathways around salicortin, the major salicinoid of many willow genotypes.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Antineoplastic Agents, Phytogenic / chemistry
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Antineoplastic Agents, Phytogenic / isolation & purification
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Antineoplastic Agents, Phytogenic / pharmacology*
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Antineoplastic Agents, Phytogenic / therapeutic use
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Benzyl Alcohols / chemistry
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Biosynthetic Pathways / genetics
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Cell Line, Tumor
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Drug Screening Assays, Antitumor
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Glucosides / biosynthesis
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Glucosides / chemistry
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Humans
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Inhibitory Concentration 50
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Neoplasms / drug therapy*
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Plant Bark / chemistry
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Plant Bark / metabolism
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Salix / chemistry*
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Salix / genetics
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Salix / metabolism
Substances
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Antineoplastic Agents, Phytogenic
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Benzyl Alcohols
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Glucosides
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salicin
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salicortin